I see similarities in this with my life during the same time frame as yours. Before I begin I would like to offer my condolences with the passing of your dad.
The mid 1990s for me was just school and partying. Not taking life too seriously. But then in 1996-1997, never liking school because I couldnt do what I really wanted to do with my life, I too started my career in more or less in the same time frame as yours. I opened up my restaurant. I dropped university to do so, never finishing and getting my degree (in marketing)I decided to work long and hard hours (in my own business at least) to compensate for the lack of a bachelors or even a masters degree.
Another similarity being that I too, had dreams about my career path that never panned out the way I wanted so I had to settle for something else. That ultimately did pan out. And Im assuming your career path is ultimately successful too from what Im understanding with our short conversations we have in these forums.
I still partied hard when I first opened up my restaurant as I was still a young man. And single. Boy, I wasnt mature during that time. Mature enough to own and manage and work my restaurant with my partner, and responsible enough not to blow all my money on partying and girls, but definitely not marriage material. (this is where I may differ from you...and Im sorry your engagement to your fiance fell apart...but maybe for the better? ) Then the new millennium came and just like that, I was ready to settle down. And I met my now, wifey. My restaurant had established itself in the community as a great place for a quick bite to to eat and I was ready to be a man. And I had to learn fast that a wife...is NOT your mommy...
I did have a hiccup along the way as I opened up a second restaurant. A Greek and Italian cuisine themed restaurant, as opposed to this one which ia a fast food joint, that...failed. This was a decade ago. Like you, I had a "start-up" that failed...
My dad passed away in 2006, about a decade after your passing of your dad.
Although my life may not have happened like yours exactly like yours, philosophically, its similar in a similar time frame.
I too, am excited to see what the next decade will bring.
As long as we have, what the French call, "La joie de vivre" and we will both be fine.